7-Hydroxycoumarin glucuronide sodium salt - ≥98% , CAS No.168286-98-4

CAS: 168286-98-4 Cat. No.: H338882 Formula: C₁₅H₁₃NaO₉ Peso molecolare: 360.25 Numero EC: 634-111-6 PubChem CID: 23675380

GRADE & PURITY ≥98%

Synonyms

7-Hydroxycoumarin glucuronide sodium salt | 7-Hydroxy coumarin glucuronide (sodium salt) | A-D-Glucuronide Sodium Salt | MFCD00674902 | 7-Hydroxy Coumarin beta-D-Glucuronide Sodium Salt | 7-Hydroxycoumarin glucuronide sodium salt is known as a 7-hydroxy c

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

Panoramica

7-Hydroxycoumarin glucuronide sodium salt is a labelled metabolite of Coumarin and 7-hydroxycoumarin phase II. 7-Hydroxycoumarin glucuronide sodium salt can be used as a standard for the analysis of 7-hydroxy coumarin metabolism. 7-Hydroxycoumarin glucuronide sodium salt was one of the eventually formed metabolites following a 1 hour incubation experiment with individual probe substrates, such as Chlorzoxazone and 7-hydroxycoumarin. The measured concentration of formed 7-Hydroxycoumarin glucuronide sodium salt can be indicative of the presence of UGT enzyme after exposure of HepaRG to the original probe substrate. 7-Hydroxycoumarin glucuronide sodium salt was undetectable in an LC-MS/MS analysis test in AR-CALUX.

Application：

7-Hydroxycoumarin glucuronide sodium salt can be used as a standard for the analysis of 7-hydroxycoumarin metabolites；Phase II (UDP-GT) metabolite of 7-hydroxycoumarin；Useful as a pharmacokinetic standard in metabolic studies.

Specifications

Sinonimi

7-Hydroxycoumarin glucuronide sodium salt | 7-Hydroxy coumarin glucuronide (sodium salt) | A-D-Glucuronide Sodium Salt | MFCD00674902 | 7-Hydroxy Coumarin beta-D-Glucuronide Sodium Salt | 7-Hydroxycoumarin glucuronide sodium salt is known as a 7-hydroxy c

Specifiche e purezza

≥98%

Condizioni di conservazione di stoccaggio

Store at 2-8°C,Argon charged

Spedito in

Wet ice

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Purezza

≥98%

Nomi e identificatori

Pubchem Sid

504769604

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/504769604

Sorrisi canonici

C1=CC(=CC2=C1C=CC(=O)O2)OC3C(C(C(C(O3)C(=O)[O-])O)O)O.[Na+]

IUPAC Name

sodium;(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(2-oxochromen-7-yl)oxyoxane-2-carboxylate

InChIKey

SKHLGBDGEPDEME-KSOKONAESA-M

INCHI

1S/C15H14O9.Na/c16-9-4-2-6-1-3-7(5-8(6)23-9)22-15-12(19)10(17)11(18)13(24-15)14(20)21;/h1-5,10-13,15,17-19H,(H,20,21);/q;+1/p-1/t10-,11-,12+,13-,15+;/m0./s1

Isomeri SMILES

C1=CC(=CC2=C1C=CC(=O)O2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)C(=O)[O-])O)O)O.[Na+]

WGK Germania

3

PubChem CID

23675380

Peso molecolare

360.25

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Classe Coumarins and derivatives
      • Subclass Coumarin glycosides

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Classe: Coumarins and derivatives
• Subclass: Coumarin glycosides
• Intermediate Tree Nodes: Not available
• Direct Parent: Coumarin glycosides
• Alternative Parents: Phenolic glycosides O-glucuronides O-glycosyl compounds 1-benzopyrans Pyranones and derivatives Beta hydroxy acids and derivatives Benzenoids Oxanes Monosaccharides Heteroaromatic compounds Secondary alcohols Carboxylic acid salts Lactones Polyols Carboxylic acids Acetals Oxacyclic compounds Monocarboxylic acids and derivatives Hydrocarbon derivatives Organic sodium salts Carbonyl compounds Organic oxides Organic cations
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Coumarin-7-o-glycoside - Coumarin o-glycoside - Phenolic glycoside - 1-o-glucuronide - O-glucuronide - Glucuronic acid or derivatives - Glycosyl compound - O-glycosyl compound - Benzopyran - 1-benzopyran - Beta-hydroxy acid - Pyranone - Benzenoid - Pyran - Hydroxy acid - Oxane - Monosaccharide - Heteroaromatic compound - Carboxylic acid salt - Secondary alcohol - Lactone - Organic alkali metal salt - Organoheterocyclic compound - Carboxylic acid derivative - Carboxylic acid - Acetal - Polyol - Monocarboxylic acid or derivatives - Oxacycle - Organic oxygen compound - Organic sodium salt - Organic oxide - Hydrocarbon derivative - Organic salt - Carbonyl group - Organooxygen compound - Alcohol - Organic cation - Aromatic heteropolycyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as coumarin glycosides. These are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Proprietà chimiche e fisiche

• Solubilità: DMSO, Water (Slightly, Heated, Sonicated)
• Sensibilità: Moisture Sensitive
• Peso molecolare: 360.250 g/mol
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 3
• Exact Mass: 360.046 Da
• Monoisotopic Mass: 360.046 Da
• Topological Polar Surface Area: 146.000 Ų
• Heavy Atom Count: 25
• Formal Charge: 0
• Complexity: 539.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 2

XLogP3

Application Protocols

Examples below are provided as literature-style guidance and should be optimized per laboratory setup. They are not validated specifications for this item.

A) β-Glucuronidase activity assay (fluorescence):

• Reagents: 50 mM sodium acetate buffer pH 5.5; enzyme (β-glucuronidase, e.g., from E. coli); 7-hydroxycoumarin glucuronide sodium salt.
• Setup (96-well): Add 90 µL buffer + 10 µL substrate (final 10 µM). Equilibrate at 37 °C. Initiate with enzyme to desired U/mL.
• Read: Kinetic mode, Ex 360 nm/Em 455 nm, 30–60 min. Include no-enzyme and no-substrate controls; calibrate with known umbelliferone standards.

B) LC–MS calibration curve (metabolite standard):

• Stock: Prepare ~1 mM in water (verify solubility); serially dilute in 0.1% formic acid in water.
• Injection: LC–MS/MS in negative ESI; monitor characteristic glucuronide transitions (optimize empirically).
• Notes: Use matrix-matched standards for quantitative bioanalysis; include at least 6 levels spanning expected concentrations.

C) Solution stability check:

• Conditions: Incubate aliquots at pH 6.0, 7.4, and 8.0 at 25 and 37 °C.
• Sampling: 0, 1, 2, 4, 8, 24 h; analyze by HPLC with fluorescence or MS to monitor aglycone release.

Adjust concentrations, pathlengths, and gain to avoid inner-filter effects and detector saturation.

Biological Roles

Literature context (not product specifications or claims):

• Phase II metabolism: 7-Hydroxycoumarin is a prototypical UGT substrate. Conjugation with D-glucuronic acid via UDP-glucuronic acid yields the O-glucuronide, markedly enhancing water solubility and facilitating renal/biliary excretion.
• Transport and disposition: The anionic glucuronide can interact with organic anion transporters (OATs/MRPs) in biological systems (reported for many glucuronides; specific transporter profiles vary by substrate).
• Enzymatic cleavage: β-Glucuronidase present in microbes and mammalian tissues can hydrolyze O-glucuronides, regenerating the aglycone (umbelliferone) and D-glucuronic acid; this underpins assay use.
• Fluorescence reporting: The aglycone umbelliferone exhibits strong blue fluorescence, making the glucuronide a pro-fluorophore that becomes highly emissive upon enzymatic cleavage.
• Model metabolite: Serves as a reference metabolite in studies of xenobiotic glucuronidation, enterohepatic cycling, and deconjugation processes.

Note: These roles describe typical biochemical behavior of umbelliferone and its glucuronide in research contexts. No medical or clinical claims are made; for research use only.

Buffer Applications

This product is not used as a buffering agent. It is an analyte/substrate employed within buffers.

Practical notes (literature/practice):

• Choose neutral buffers (e.g., 50 mM phosphate, pH 6.8–7.4; 50 mM HEPES, pH 7.2–7.6) for preparing stocks and running assays to limit non-enzymatic hydrolysis.
• For β-glucuronidase assays, mildly acidic buffers (e.g., acetate pH 4.5–6.0) are sometimes used to match enzyme optima; include appropriate blanks/controls to account for any background cleavage.

Green Alternatives

As a water-soluble analyte and enzymology standard, this compound already supports aqueous, solvent-minimizing workflows.

Greener practice suggestions (literature/practice):

• Aqueous-only preparations: Prepare and use water/buffer stocks instead of DMSO-based stocks to avoid aprotic solvent waste and potential enzyme inhibition.
• Benign buffers: Favor phosphate, HEPES, or acetate at moderate ionic strength; avoid excessive organic modifiers in fluorescence assays.
• Room-temperature reactions: Many enzymatic and hydrolysis assays proceed at ambient to 37 °C, reducing heating needs.
• Miniaturization: Use microplate formats (96/384-well) to cut reagent consumption and waste.
• Waste segregation: Collect minimal volumes of aqueous waste; avoid adding halogenated solvents unless required for extraction.

Comparison to alternatives (literature):

• 7-Hydroxycoumarin glucuronide vs 4-methylumbelliferyl-β-D-glucuronide (4-MUG):
  • 4-MUG is a widely used fluorogenic substrate with very high sensitivity; however, it often requires DMSO stocks due to lower aqueous solubility compared with sodium glucuronides.
  • The sodium salt of 7-hydroxycoumarin glucuronide offers excellent water solubility, enabling fully aqueous handling and improved green metrics.

Trade-offs:

• The released fluorophore’s quantum yield and excitation profile may differ from 4-MU; select the substrate that best matches available optics while maintaining an aqueous, low-solvent protocol.

Pharmaceutical Uses

No therapeutic or clinical uses are claimed. Research use only.

Relevant roles in pharmaceutical R&D and manufacturing (literature/practice):

• Reference standard for analytical methods in drug metabolism and bioanalysis (e.g., LC–MS quantitation of glucuronide metabolites).
• System suitability and recovery controls for sample deconjugation workflows using β-glucuronidase.
• In vitro UGT screening: Benchmark substrate/metabolite pair for qualifying UDP-glucuronosyltransferase activity in microsomes, S9, or recombinant systems.
• Stability studies: Model compound for evaluating hydrolysis kinetics in formulation-relevant pH ranges.

Regulatory notes:

• Pharmacopeial monographs for this specific glucuronide are not commonly available; users should establish internal reference material characterization (purity assignment, identity confirmation, and storage conditions) as per lab SOPs.

Physical Properties

Item-specific physicochemical specifications (mp, bp, UV cut-off, metals, water, etc.): Not specified for this item; refer to CoA/Spec Sheet.

Literature/general properties for guidance only (not product specifications):

• Physical state/appearance: Typically an off-white to pale solid; may be hygroscopic (literature, common for sodium glucuronides).
• Molecular weight: ~360.25 g/mol (literature, see Structure & Identity).
• Acid/base character: Carboxylate sodium salt; behaves as a strong electrolyte in water. The phenolic aglycone is masked by glycosidic linkage.
• Solubility: High in water and aqueous buffers; sparing to low in most anhydrous organic solvents (literature trend for ionic glucuronides).
• Partitioning: Expected low logP/negative logD in neutral water due to ionic carboxylate (literature expectation).
• UV/fluorescence behavior: The conjugate itself shows weak fluorescence; enzymatic or chemical hydrolysis releases 7-hydroxycoumarin (umbelliferone), which is strongly fluorescent (Ex ~325–365 nm, Em ~450–460 nm; literature values).
• Thermal stability: Organic glucuronides can decompose or hydrolyze upon prolonged heating; gentle drying and refrigerated storage are recommended (literature guidance).

Note: Exact numerical values (mp, solubility limits, extinction coefficients, refractive index, water content) are not specified for this item; consult the CoA/SDS for definitive data.

Quality and Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

Interpretation and implications (general guidance):

• For enzyme assays or bioanalytical applications, users typically require high chemical purity and low inorganic residue to minimize background fluorescence and matrix effects. Verify by HPLC/UPLC purity and NMR where applicable.
• If using as a reference standard (e.g., in metabolism studies or LC–MS method development), confirm identity via HRMS and document traceability (e.g., to a certified lot with assigned purity).
• Absence of a stated stabilizer suggests the neat solid; however, some glucuronides benefit from inert-atmosphere packaging to limit hydrolysis/oxidation—consistent with this item being argon charged.
• If low-UV or LC–MS suitability is critical, check the CoA for any UV-absorbing impurities and confirm residual solvent levels.

Recommended user QC (best practice):

• Record appearance on receipt; verify lot-specific purity by HPLC and identity by MS/NMR as needed for regulated workflows.
• Assess solution stability in intended buffer by short-term stress (pH/temperature) and monitor for aglycone formation (umbelliferone) via fluorescence or LC–MS.

Reaction and Applications

This material is primarily used as a biochemical probe/standard rather than as a synthetic reagent.

Key laboratory applications (literature/practice):

• β-Glucuronidase substrate/standard: Upon enzymatic hydrolysis of the O-glucuronide, 7-hydroxycoumarin (umbelliferone) is released, producing strong blue fluorescence (Ex ~325–365 nm, Em ~450–460 nm). Useful for monitoring β-glucuronidase activity, optimizing enzyme conditions, or validating sample deconjugation steps.
• UGT metabolism studies: Serves as an authentic phase II metabolite of umbelliferone; applied as a calibration standard in LC–MS workflows assessing UDP-glucuronosyltransferase (UGT) activity and glucuronidation kinetics.
• Method development: Reference material for solid-phase extraction (SPE) recovery optimization and matrix deconjugation validation in biological fluids.

Practical notes:

• For kinetic assays, avoid buffers below pH ~5.5 to minimize non-enzymatic hydrolysis. Maintain ionic strength typical of enzyme buffers (50–150 mM).
• Fluorescence readouts require appropriate bandpass settings and inner-filter minimization; include blanks without enzyme to correct for background.
• For LC–MS quantitation, consider stable-isotope internal standards if available; otherwise, use matrix-matched calibration.

Related reactions (literature):

• Acid/base-catalyzed hydrolysis of O-glucuronides.
• Enzymatic cleavage by bacterial or mammalian β-glucuronidase to yield umbelliferone and D-glucuronic acid.

Reaction Conditions

Guidance below summarizes typical literature conditions for common uses; these are not product specifications.

1. Enzymatic hydrolysis by β-glucuronidase (to release umbelliferone):

• Buffer: 50 mM acetate or phosphate, pH 5.0–6.5 (optimum depends on enzyme source)
• Temperature: 30–37 °C
• Substrate concentration: 1–200 µM (optimize to stay below Km and within linear fluorescence range)
• Enzyme loading: e.g., 10–1000 U/L depending on source/activity
• Time: 10–120 min with time-course sampling
• Readout: Fluorescence Ex 325–365 nm, Em 450–460 nm; include blanks without enzyme

2. UGT-mediated formation (from umbelliferone):

• System: Liver microsomes/S9 or recombinant UGTs
• Cofactors: 2–5 mM UDPGA; 5 mM MgCl2; optional alamethicin activation
• Buffer: 50 mM phosphate or Tris, pH 7.4
• Umbelliferone: 1–200 µM
• Temperature: 37 °C; Time: 5–60 min; Quench: ice-cold ACN/MeOH
• Analysis: LC–MS/MS with negative ESI for the glucuronide anion

3. Non-enzymatic stability checks:

• pH range: 5–8 for minimal degradation; avoid <pH 4 and >pH 9 for extended periods
• Storage solutions: Keep chilled and protected from light; analyze promptly to limit hydrolysis.

Safety and Handling

Authoritative safety information must be taken from the product SDS.

Item-specific hazard classification (GHS, signal word, H/P statements, pictograms): Not specified for this item; refer to SDS.

General handling guidance for glucuronide sodium salts (literature/practice):

• Expected hazards: Low acute toxicity but may cause skin/eye/respiratory irritation as a fine organic powder. Avoid inhalation and contact.
• PPE: Lab coat, safety glasses, and nitrile gloves. Work in a fume hood or well-ventilated area when handling powders.
• Storage incompatibilities: Avoid strong oxidizers. Strong acids can liberate the free glucuronic acid form and promote hydrolysis; strong bases can cleave glycosidic or lactone bonds upon heating or prolonged exposure.
• Special risks: Glycosidic linkages are susceptible to acid-catalyzed hydrolysis; moisture and CO2 uptake may occur due to ionic nature. Product is supplied argon charged and should be kept tightly closed to minimize oxidative or hydrolytic degradation.
• First aid overview: In case of contact, rinse affected area with water for ≥15 min; remove contaminated clothing. If inhaled, move to fresh air. If ingested, rinse mouth with water. Seek medical attention if symptoms persist. Defer to SDS for detailed measures.
• Spill response: Avoid dust generation; collect by gentle sweeping or HEPA vacuum, then wipe with damp disposable towels. Dispose according to local regulations for laboratory chemical waste.

Solvent Selection

This compound is an ionic organic salt (sodium carboxylate) and is best handled in aqueous media.

• Primary solvent: Water and aqueous buffers (e.g., phosphate, acetate, HEPES). Rapid dissolution is expected.
• pH considerations: Glycosidic bonds are susceptible to acid-catalyzed hydrolysis; maintain pH ~6–8 for storage/handling unless intentional hydrolysis is desired. Very basic conditions can also promote degradation over time.
• Co-solvents: If organic content is needed (e.g., for chromatography make-up), use small percentages of MeOH or ACN. DMSO stocks are generally unnecessary and may complicate enzymology; prefer water.
• Miscibility profile (literature):
  • Water: miscible, high solubility
  • Alcohols (MeOH, EtOH): moderate to good (reduced versus water)
  • Aprotic solvents (ACN, DMF, DMSO): variable; ionic nature limits solubility without water
  • Nonpolar solvents (EtOAc, hexanes, toluene): insoluble

Comparison (literature):

• Versus the aglycone (umbelliferone): the glucuronide is far more water soluble and far less fluorescent; the aglycone favors organic solvents but is less suitable for aqueous enzymatic systems.

Practical tips:

• Prepare fresh aqueous stocks for assays; filter (0.22 µm) if needed.
• Avoid strong acids in solution unless hydrolysis is intended; use neutral buffers for storage.

Storage and Reconstitution

Item-specific instructions:

• Storage Conditions (provided): Store at 2–8 °C, argon charged.
• Shipped In (provided): Wet ice.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.

General guidance (supplemental; not a specification):

• Container: Keep tightly sealed under inert gas to limit moisture/CO2 uptake and hydrolysis.
• Light protection: Store in amber vials or protect from light to minimize photodegradation of the coumarin core.
• Reconstitution: Prefer ultrapure water or neutral buffer (e.g., 10–50 mM phosphate, pH 7.0). Start at 1–10 mM stock, adjusting to solubility and assay needs.
• Filtration: If required, sterile-filter through 0.22 µm PTFE/PES.
• Aliquoting: Prepare single-use aliquots; avoid repeated freeze–thaw of solutions. For longer storage of solutions, freeze at −20 to −80 °C and verify stability empirically (monitor for umbelliferone formation).
• Shelf life: Not specified for this item; refer to CoA/Spec Sheet.

Research Use Note: For research use only. Consult the CoA and SDS for lot-specific stability and safety information before use.

Structure and Identity

A glucuronide conjugate of the fluorescent coumarin aglycone umbelliferone (7-hydroxycoumarin), supplied as the sodium salt of the glucuronic acid carboxylate.

• Product Name (SKU): 7-Hydroxycoumarin glucuronide sodium salt (H338882)
• CAS: 168286-98-4
• PubChem CID: 23675380
• InChIKey (as provided): 338215
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: C15H13O9Na (literature, typical for the sodium salt of umbelliferone β-D-glucuronide)
• Molecular weight: ~360.25 g/mol (literature, derived from formula above)

Structural features (general description):

• Core scaffold: Coumarin (1-benzopyran-2-one) ring system bearing a 7-hydroxy substituent.
• Conjugation: The phenolic oxygen at C-7 is O-glycosidically linked to β-D-glucuronic acid; the carboxylate of glucuronic acid is present as the sodium salt.
• Functional groups: Lactone (coumarin), aryl ether (O-glycosidic bond), secondary alcohols on sugar, and a carboxylate (as Na+ salt).
• Stereochemistry: The glucuronic acid moiety is typically β-D configuration at the anomeric center (literature).

2D structure in words (literature): A benzopyran-2-one ring with a para-oriented phenolic oxygen (position 7) forming an O-glycosidic bond to the anomeric carbon of a D-glucuronic acid ring; the sugar bears multiple axial/equatorial hydroxyls and a carboxylate (sodium) at C-6.

Synthetic Utility

While primarily a biochemical standard, limited synthetic or preparative utilities exist (literature/practice):

• Pro-fluorophore precursor: Controlled hydrolysis (enzymatic or chemical) yields 7-hydroxycoumarin (umbelliferone) in aqueous media, useful for calibration of fluorescence detection systems.
• Glycoconjugate model: Serves as a model O-glycoside for studying protecting-group-free manipulations, hydrolysis kinetics, and stability trends of aryl O-glucuronides.
• Analytical derivatization: The glucuronide can be used to benchmark derivatization or enzymatic deconjugation steps preceding GC/LC analyses of phenolic metabolites.

Considerations:

• The lactone ring of the coumarin can undergo base-catalyzed opening under strong alkaline conditions; preserve integrity by neutral pH handling.
• Use aqueous-compatible purification (e.g., reversed-phase SPE/HPLC) if processing solutions; avoid strong acids that promote unwanted hydrolysis.

Target Specificity

This product is a small-molecule metabolite standard, not a biological binding reagent or antibody. No antigen/epitope, species reactivity, clone, or isotype are applicable.

Domande frequenti

What is the purity of this product?

This product is supplied at ≥98% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at 2–8 °C under argon. It is supplied under an argon blanket; reseal under inert gas after each use.

How is this product shipped?

This product ships chilled on wet ice. Unpack on arrival and transfer it to the storage condition stated above.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 168286-98-4, the molecular formula is C15H13NaO9, and the molecular weight is 360.25 g/mol. InChIKey SKHLGBDGEPDEME-KSOKONAESA-M.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.